Fashion sense from the ultra-wealthy: What understated luxury really looks like

By Kristen Oliveri

I’ve never considered myself a fashionista. In fact, it wasn’t until my mid-30s that I truly began to understand my own sense of style, discovering the colors that complemented my palette, letting go of trends that didn’t serve me, and choosing silhouettes that genuinely flattered my body. As I matured and became more intentional with my wardrobe choices, something else happened too: I started paying closer attention to the fashion sensibilities of my ultra-high-net-worth clients and friends.

At galas, industry events, or even casual coffee meetings in major cities, I quietly observed what the most stylish among them were actually wearing. Around that time, the trendy term “stealth wealth” began circulating, but what I was seeing wasn’t a trend. It was a lifestyle philosophy.

What became clear was this: while a discreet label might appear here or there, the look was never about logos. It was about style. Fit. Effortless elegance. Nothing flashy. Nothing performative. Just confidence paired with great tailoring.

Years ago, a colleague and devoted fashion lover gave me a piece of advice that changed everything. Over drinks one evening, I asked her the question I had always wanted to:

How do you always look so put-together? Are you constantly buying designer?

She laughed and confessed her secret: “You only need one or two high-end signature pieces. Everything else can be basic staples.”

She told me her favorite places to shop for those staples were stores like Zara and H&M. The key, she said, was simple: choose a color palette that flatters you (mine is clearly camels, browns, whites, and warm neutrals), and invest in well-fitting foundational pieces that allow for endless mixing and matching.

Over time, I noticed something similar among my rising-gen clients and peers. Their wardrobes weren’t loud or logo-heavy. Instead, they were intentionally composed: a beautifully structured blazer, a well-placed scarf, an exquisite handbag, a pair of impeccably made Italian shoes. Every look felt considered yet effortless.

Less was truly more.

Then the TV show Succession hit the cultural conversation and validated everything I’d been tracking in real life. Suddenly, everyone was talking about stealth wealth—the quiet luxury of a man in a simple baseball cap that happened to be Ralph Lauren Purple Label, or the understated sweater paired with a $50,000 watch. The verdict was unanimous: understated luxury wasn’t just a style; it was a statement.

After having my two children and returning to something resembling my pre-baby body, I decided it was time for a reset. I stood in my closet and made a ruthless edit.

Too many patterns? Gone.

Poor fit? Gone.

Trendy without staying power? Definitely gone.

What remained was the opportunity to rebuild intentionally. I started assembling a wardrobe that felt aligned with who I was now: blazers that fit beautifully, the perfect trousers, and an assortment of classic tops (button-downs, camisoles, bodysuits) that could work for any occasion. And thanks to the rise of remote work and a more relaxed professional dress code, I found myself more comfortable, polished, and confident than in any previous iteration of my wardrobe.

What I learned from the ultra wealthy, and from my own evolution, is that understated luxury isn’t about owning more. It’s about choosing well. It’s about fit, quality, longevity, and the quiet kind of confidence that doesn’t need to announce itself.

A curated wardrobe may begin in the closet, but the mindset behind it, intentionality, refinement, and authenticity, is the real luxury.